Geosmithia fungi are little known symbionts of bark beetles. Secondary metabolites of lilac colored species G. lavendula and other nine Geosmithia species were investigated in order to elucidate their possible role in the interactions of the fungi with environment. Hydroxylated anthraquinones (yellow, orange, and red pigments), were found to be the most abundant compounds produced into the medium during the submerged cultivation. Three main compounds were identified as 1,3,6,8-tetrahydroxyanthraquinone (1), rhodolamprometrin (1-acetyl-2,4,5,7-tetrahydroxyanthraquinone; 2), and 1-acetyl-2,4,5,7,8-pentahydroxyanthraquinone (3). Compounds 2 and 3 (representing the majority of produced metabolites) inhibited the growth of G+-bacteria Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration of 64-512 microg/mL. Anti-inflammatory activity detected as inhibition of cyclooxygenase-2 was found only for compound 3 at 1 and 10 microg/mL. Compound 2 interfered with the morphology, compound 3 with cell-cycle dynamics of adherent mammalian cell lines.

• MeSH
• anthrachinony chemie   metabolismus   farmakologie   MeSH
• antibakteriální látky chemie   metabolismus   farmakologie   MeSH
• antiflogistika nesteroidní chemie   metabolismus   farmakologie   MeSH
• Bacillus subtilis účinky léků   MeSH
• biologické pigmenty chemie   metabolismus   farmakologie   MeSH
• biotechnologie metody   MeSH
• buněčný cyklus účinky léků   MeSH
• Ficus parazitologie   MeSH
• HeLa buňky MeSH
• hydroxylace MeSH
• Hypocreales růst a vývoj   metabolismus   MeSH
• inhibitory cyklooxygenasy chemie   metabolismus   farmakologie   MeSH
• lidé MeSH
• nosatcovití mikrobiologie   fyziologie   MeSH
• spory hub růst a vývoj   metabolismus   MeSH
• Staphylococcus aureus účinky léků   MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 1-acetyl-2,4,5,7-tetrahydroxyanthraquinone MeSH Prohlížeč
• 1-acetyl-2,4,5,7,8-pentahydroxyanthraquinone MeSH Prohlížeč
• 1,3,6,8-tetrahydroxyanthraquinone MeSH Prohlížeč
• anthrachinony MeSH
• antibakteriální látky MeSH
• antiflogistika nesteroidní MeSH
• biologické pigmenty MeSH
• inhibitory cyklooxygenasy MeSH

Degradation of anthocyanins involves scission of the flavonoid skeleton yielding 2,4,6-trihydroxybenzaldehyde (phloroglucinaldehyde, PGA) and a phenolic acid. However, the process is not finished with the formation of PGA, as the consequent condensation of two PGA molecules providing colored hydroxylated anthraquinones was observed for the first time. This process was studied using a combination of preparative column chromatography, nuclear magnetic resonance, liquid chromatography/high resolution tandem mass spectrometry (LC/HRMS2), and quantum calculations using density functional theory. 1,3,5,7-tetrahydroxyanthraquinone (anthrachrysone) and its isomers were found to rise during heating (95 °C) in a buffered PGA model solution (phosphate buffer, pH 7). These compounds were detected in heated red wine after an increase of its pH value. The concentration of the identified anthrachrysone in the red wine reached 0.01 mg·L-1. Presence of those compounds could therefore indicate involvement of certain steps in the processing of plant materials rich in anthocyanins (e.g., utilization of a higher temperature and/or reduction of acidity) or long-term transformation of anthocyanins (potentially, for instance, in archaeological findings such as wine or fruit residues). Additionally, measurement of wine-soil suspensions proved an increase of their pH to the values suitable for anthocyanin cleavage (neutral to slightly alkaline; reached using soil from archaeologically well-known Bull Rock Cave). Although not found in artificially prepared samples (imitations) or authentic materials so far, according to our results the above mentioned conditions are suitable for the formation of tetrahydroxylated anthraquinone derivatives and their monitoring would be beneficial.

• Klíčová slova
• anthocyanin, degradation, hydroxyanthraquinone, phloroglucinaldehyde, wine,
• MeSH
• analýza potravin * metody   MeSH
• anthokyaniny chemie   MeSH
• anthrachinony analýza   chemie   MeSH
• chromatografie kapalinová MeSH
• hmotnostní spektrometrie MeSH
• molekulární modely MeSH
• molekulární struktura MeSH
• víno analýza   MeSH
• vysokoúčinná kapalinová chromatografie MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• anthokyaniny MeSH
• anthrachinony MeSH

Lilac coloured species of Geosmithia lavendula produce a mixture of polyhydroxylated anthraquinones under condition of submerged fermentation. Three pigments had been isolated and identified earlier as a 1,3,6,8-tetrahydroxyanthraquinone (compound 7), rhodolamprometrin (1-acetyl 2,4,5,7-tetrahydroxyanthraquinone; compound 5), and 1-acetyl 2,4,5,7,8-penthahydroxyanthraquinone (compound 4). A new HPLC method was developed for the separation of three known and ten new anthraquinone pigments. In addition, five new pigments were determined by FTMS as coeluting impurities. The analyses were performed on a reversed phase column using gradient elution with a mobile phase system consisting of phosphate buffer (50 mM; pH=2.0) and acetonitrile. The structure evaluation was based namely on FTMS and UV-VIS spectrometry. The developed procedure was used for the determination of individual anthraquinones in fermentation broth of G. lavendula after 14 days of cultivation. The extractable amount and LOQ (both in μg ml(-1)) for the two main pigments from G. lavendula are 50.02 and 2.15 for compound 4, and 63.77 and 2.75, for compound 5, respectively.

• MeSH
• anthrachinony analýza   chemie   MeSH
• chromatografie s reverzní fází MeSH
• fermentace MeSH
• Hypocreales chemie   MeSH
• lineární modely MeSH
• methanol MeSH
• reprodukovatelnost výsledků MeSH
• senzitivita a specificita MeSH
• tandemová hmotnostní spektrometrie metody   MeSH
• vysokoúčinná kapalinová chromatografie metody   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• anthrachinony MeSH
• methanol MeSH

Mutagenicity of anthraquinone aglycones from Rubia tinctorum L. (Rubiaceae) was examined using the somatic mutation and recombination test in Drosophila melanogaster. Larvae heterozygous for recessive wing trichome mutations, multiple wing hairs (mwh), and flare (flr3) were exposed to test compounds and wings of emerged mwh/flr3 females were inspected for the presence of phenotypically mutant mosaic spots. No significant increase in the frequency of mutant spots was observed after the treatment of Drosophila larvae with pure alizarin, xanthopurpurin, and lucidin, or with the crude mixture of anthraquinone aglycones. In contrast, the naphthohydroquinone mollugin induced mainly single spots that can originate either from somatic mutation or from mitotic recombination. Twin spots, consisting of both the mwh and flr3 subclones and originating exclusively from mitotic recombination, were also enhanced, but the increase was only marginally significant. We suggest that mollugin exhibits both the mutagenic and recombinagenic activities.

• MeSH
• anthrachinony izolace a purifikace   farmakologie   toxicita   MeSH
• Drosophila melanogaster účinky léků   genetika   růst a vývoj   MeSH
• kořeny rostlin chemie   MeSH
• křídla zvířecí účinky léků   MeSH
• larva účinky léků   genetika   MeSH
• léčivé rostliny chemie   MeSH
• molekulární struktura MeSH
• mutageny izolace a purifikace   farmakologie   toxicita   MeSH
• pyrany izolace a purifikace   farmakologie   toxicita   MeSH
• rekombinace genetická účinky léků   MeSH
• Rubiaceae chemie   MeSH
• testy genotoxicity MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• srovnávací studie MeSH
• Názvy látek
• anthrachinony MeSH
• mutageny MeSH
• pyrany MeSH
• rubimaillin MeSH Prohlížeč

Microbial strains isolated from extreme and understudied environments, such as caves, are still poorly investigated for the production of bioactive secondary metabolites. Investigation of the ethyl acetate extract from the growth medium produced by the soil-derived fungus Aspergillus sp. SDC28, isolated from a Brazilian cave, yielded two anthraquinones: versicolorin C (1) and versiconol (2). The complete assignment of nuclear magnetic resonance and mass spectroscopic data of 1 and 2 was performed for the first time. Moreover, the yet unreported absolute configuration of both compounds was unambiguously established by analysis of experimental and theoretical electronic circular dichroism data. Vibrational circular dichroism was also applied to confirm the absolute stereochemistry of 2. Compounds 1 and 2 showed cytotoxic activity against human ovarian cancer cells (OVCAR3).

• Klíčová slova
• anticancer, aromatic metabolites, extremophiles, polyketides, soil-derived fungus,
• MeSH
• anthrachinony farmakologie   MeSH
• apoptóza MeSH
• Aspergillus chemie   metabolismus   MeSH
• cirkulární dichroismus MeSH
• jeskyně * MeSH
• lidé MeSH
• molekulární struktura MeSH
• nádorové buněčné linie MeSH
• nádory vaječníků * MeSH
• oligodeoxyribonukleotidy MeSH
• půda MeSH
• thionukleotidy MeSH
• vztahy mezi strukturou a aktivitou MeSH
• Check Tag
• lidé MeSH
• ženské pohlaví MeSH
• Publikační typ
• časopisecké články MeSH
• Geografické názvy
• Brazílie MeSH
• Názvy látek
• anthrachinony MeSH
• oligodeoxyribonukleotidy MeSH
• půda MeSH
• Sd(C)28 MeSH Prohlížeč
• thionukleotidy MeSH

• MeSH
• anthrachinony farmakologie   toxicita   MeSH
• lidé MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• přehledy MeSH
• Názvy látek
• anthrachinony MeSH

This study deals with the identification of anthraquinoid molecular markers in standard dyes, reference lakes, and paint model systems using a micro-invasive and nondestructive technique such as matrix-assisted laser desorption/ionization time-of-flight-mass spectrometry (MALDI-ToF-MS). Red anthraquinoid lakes, such as madder lake, carmine lake, and Indian lac, have been the most widely used for painting purposes since ancient times. From an analytical point of view, identifying lakes in paint samples is challenging and developing methods that maximize the information achievable minimizing the amount of sample needed is of paramount importance. The employed method was tested on less than 0.5 mg of reference samples and required a minimal sample preparation, entailing a hydrofluoric acid extraction. The method is fast and versatile because of the possibility to re-analyze the same sample (once it has been spotted on the steel plate), testing both positive and negative modes in a few minutes. The MALDI mass spectra collected in the two analysis modes were studied and compared with LDI and simulated mass spectra in order to highlight the peculiar behavior of the anthraquinones in the MALDI process. Both ionization modes were assessed for each species. The effect of the different paint binders on dye identification was also evaluated through the analyses of paint model systems. In the end, the method was successful in detecting madder lake in archeological samples from Greek wall paintings and on an Italian funerary clay vessel, demonstrating its capabilities to identify dyes in small amount of highly degraded samples. Graphical Abstract ᅟ.

• Klíčová slova
• Anthraquinones, LDI, MALDI, Organic lakes, Singly charged double cation adducts, ToF,
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH

• MeSH
• anthrachinony farmakologie   MeSH
• Bacteria účinky léků   MeSH
• dezinsekce MeSH
• houby účinky léků   MeSH
• viry účinky léků   MeSH
• Publikační typ
• časopisecké články MeSH
• přehledy MeSH
• Názvy látek
• anthrachinony MeSH

Water, ubiquitous in analytical methods, is renowned for its fluorescence quenching properties, influencing techniques like fluorescence spectrophotometry or techniques with fluorescence detection. This study explores the impact of water (H₂O) substitution for heavy water (D₂O) on the fluorescence behavior of anthraquinones and anthracyclines. Anthraquinones and anthracyclines play crucial roles in pharmacy, serving as essential components in various therapeutic formulations, particularly in cancer treatment and other pharmacological interventions. Capillary electrophoresis (CE) with heavy water as the background electrolyte (BGE) solvent offers superior sensitivity to the separation and detection of these analytes. Experimental results demonstrate the improved detection limits and separation efficiency of selected anthraquinones rhein (RH), aloe-emodin (AE), and anthracyclines doxorubicin (DOX), epirubicin (EPI) and daunorubicine (DAU) in heavy water-based buffers, highlighting the potential of heavy water in advancing analytical chemistry.

• Klíčová slova
• Anthracyclines, Anthraquinones, Capillary electrophoresis, Fluorescence detection, Heavy water,
• MeSH
• anthrachinony * chemie   analýza   MeSH
• antracykliny analýza   chemie   MeSH
• elektroforéza kapilární * metody   MeSH
• fluorescenční spektrometrie * metody   MeSH
• limita detekce MeSH
• oxid deuteria chemie   MeSH
• voda chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• anthrachinony * MeSH
• antracykliny MeSH
• oxid deuteria MeSH
• rhein MeSH Prohlížeč
• voda MeSH

• MeSH
• anthrachinony farmakologie   MeSH
• imunita účinky léků   MeSH
• lidé MeSH
• mutageneze účinky léků   MeSH
• nádory jater chemicky indukované   MeSH
• protinádorové látky farmakologie   MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• přehledy MeSH
• Názvy látek
• anthrachinony MeSH
• protinádorové látky MeSH